Photo by Elizabeth Csanady

Search Cottages in Essex

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Compare 47 Cottages in Essex with updated reviews, rates, and availability.

NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

10.0 out of 10, Exceptional, (25)
"My husband and I stayed here for 3 nights while I recovered from a surgery. It was a perfect, peaceful cottage and beautiful neighborhood. "
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

Peaceful getaway convenient to local amenities including beach, boating & food

9.8 out of 10, Exceptional, (110)
"Bay Haven was in a great lication and property mananger was very responsive to al my questions. "
Peaceful getaway convenient to local amenities including beach, boating & food

Amazing views, short walks and quick access to USNA events/Commissioning Week and stadium.

10.0 out of 10, Exceptional, (80)
"Great spot, loved the place and the area. James was super helpful and seemed to want to do everything possible to make sure we had a great stay."
Amazing views, short walks and quick access to USNA events/Commissioning Week and stadium.

Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,

10.0 out of 10, Exceptional, (26)
"Great location and very clean property. Cyndi was responsive and a great host. Would definitely stay again."
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,

The Heron's Nest at Atlantic Marina

10.0 out of 10, Exceptional, (288)
"Great location, wonderful interactions with owners, beautiful scenery, and easy check-in"
The Heron's Nest at Atlantic Marina

Eastern Shore beach cottage get-away

10.0 out of 10, Exceptional, (133)
"This house was the cutest little place right across the street from the beach with a beautiful view. The house was clean and had all the amenities needed for our stay. We would definitely stay there again!"
Eastern Shore beach cottage get-away

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring

10.0 out of 10, Exceptional, (86)
"Our eighth stay at this property was just as good as ever. It is our home-away-from-home when visiting family in Annapolis. Highly recommended!"
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring

Oyster Cottage - walk to shops , Mainstay music venue and the Bay!

10.0 out of 10, Exceptional, (8)
"Easy and flexible check in, clean and comfortable in a great location. Darling home. "
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!

Waterfront River Cottage for 2, dog-friendly

9.2 out of 10, Wonderful, (7)
"It's a beautiful location and we enjoyed our visit."
Waterfront River Cottage for 2, dog-friendly

Chic Baltimore Retreat - 6 Mi to Downtown!

3.0 star property
Chic Baltimore Retreat - 6 Mi to Downtown!

Chesapeake Cottages- 2 Quaint Waterfront Retreats

9.6 out of 10, Exceptional, (22)
"10 family members from age 88 to 10 years old. It’s our 2nd visit and we’ve not been to any place more welcoming and peaceful. The location is just heaven and the docks and water views are just unbelievably gorgeous. It’s going to be an annual trip for our family."
The price is SARĀ 1,500
SARĀ 2,689 total
includes taxes & fees
5 May - 6 May
Chesapeake Cottages- 2 Quaint Waterfront Retreats

House w/Water Views of Rock Creek 2BA 2BA Cottage

10.0 out of 10, Exceptional, (26)
"Very quiet street, our stay was relaxing and just what we needed! "
House w/Water Views of Rock Creek 2BA 2BA Cottage

The Cottage at Merryland Farm

10.0 out of 10, Exceptional, (1)
"The host was amazing; very attentive even willing to provide tour. We lived close by for years and were back to visit family so great location as we already knew the area well. House is small as name suggests 'Cottage' wouldn't suggest more than 2 - 3 at the most. Cottage was quaint and well equipped with everything. Very quiet and safe and scenic. We would stay again if back in area "
The Cottage at Merryland Farm

Cozy Cottage

10.0 out of 10, Exceptional, (1)
"Lovely home with everything you need."
Cozy Cottage

Cozy Nautical Cottage in Annapolis w/ Beautiful Outdoor Space

8.8 out of 10, Excellent, (3)
"The owner was absolutely amazing and the cottage (inside and out) was inviting, clean and super comfortable. We wanted a relaxing place to spend time visiting with our son and we found that here. I was able to cook his favorite meals and we were able to spend time eating, watching movies, playing games and enjoying time as a family. Great location for 2-4 people."
Cozy Nautical Cottage in Annapolis w/ Beautiful Outdoor Space

Rock Creek Cottage, Waterfront, Serene Views

10.0 out of 10, Exceptional, (2)
"Absolutely amazing place for my husband and I to relax with our midshipmen. Very clean, beautifully decorated and the view on the dock each morning was stunning! Close to restaurants (loved 3 B’s Bakery) and host was awesome! "
Rock Creek Cottage, Waterfront, Serene Views

Rare find! Chic cottage, salt water heated pool May 15-Oct15.

10.0 out of 10, Exceptional, (50)
"The house was even nicer than in photos or descriptions. The house very spacious, the pool and pool area were perfect for our needs. The hosts were very gracious, communicative, and easy to work with. I would definitely recommend this property."
Rare find! Chic cottage, salt water heated pool May 15-Oct15.

Waterfront Annapolis Home: Fire Pit & Fishing Pier

3.0 star property
Waterfront Annapolis Home: Fire Pit & Fishing Pier

6 Mi to Dtwn Baltimore: Home w/ Fire Pit!

3.0 star property
6 Mi to Dtwn Baltimore: Home w/ Fire Pit!

Sunny Glen Burnie Home - On-site Water Access

3.0 star property
Sunny Glen Burnie Home - On-site Water Access
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Essex
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Essex

Fantastic 2 bedrooms apt. Harbor

4.0 star property
10.0 out of 10, Exceptional, (1)
"It was a nice place"
Fantastic 2 bedrooms apt. Harbor

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (214)
"Great property and location to everything is ideal. Would definitely book this place again. "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Distinguished Apartment Rooftop Deck

3.5 star property
10.0 out of 10, Exceptional, (7)
"We had a great stay! A fantastic building in a very convenient area. "
Distinguished Apartment Rooftop Deck
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.